How-To: Lessons from Dressing Myself

Today, some advice for the genderqueer, trans, lady-mannish, etc. people out there. Through years of dressing myself I have gained some hard-won experience on how to get menswear, or just masculinity, to work with a body that is shorter and curvier than those of many cisgendered men. Obviously,  my perspective is grounded in my body and my style-specific. If you are tall, or straight-hipped, then some of this won’t apply to you. Pick and choose which nuggets of wisdom will help you the most, and remember the cardinal rule: Fit Above All. If it looks good on you, wear it.

My rule of thumb is that I can sometimes wear women’s clothes from the waist down (underwear excepted! But that’s up to you), but from the waist up I only wear men’s. I have both men’s and women’s jeans. The skinny jeans trend has been a good thing for guys like me, since it has led to a convergence of men’s and women’s cuts. The most important thing is for jeans to fit and fit well. This can be a challenge with hips and men’s jeans. I like men’s Levi’s, though, specifically the 510 super skinnys:



However, I never wear women’s pants. Wearing pants made for women leads to a phenomenon I call, “Looking like someone’s aunt.” The cut of women’s pants is more feminine than the cut of jeans, and so I always go menswear with these.

Zara has excellent men’s pants:




Zara smocked pants.


If you are in NYC, go to Uniqlo.  They have great men’s pants (and suits, and shirts). Uniqlo can be all-around great.


Last year’s Uniqlo.


If you are short, like I am, it will be very hard to find men’s shoes in your size. My feet are a size 6 women’s, which means they are a size impossibletofind men’s. I  just look for women’s shoes that aren’t feminine: low heels, heavier soles, and not too narrow. A few that I especially like:


Frye James Wingtips.


Frye Dakota Wedge (Frye is great, obviously).


Clark’s Desert Boots (classic!).


More desert boots (so classic! get more than one color!)


I also like to wear sneakers and boat shoes more than I otherwise would, since, like jeans, they tend to be more gender-neutral. Casual often = unisex.


Sperry Topsiders (another classic).


Shirts are the most important part of my lady-man wardrobe.  This is true in part because I am short, and people are mostly only looking at the top half of my body.  It is also true because my shirts have a very important job to do (along with my binders): they have to mitigate my chest. For this reason, I have a bit of a uniform. I almost always wear a structured, tailored men’s shirt. Sometimes with an undershirt, sometimes without. Sometimes with a tie, or a cardigan, or suspenders, sometimes without. But I have found that a men’s button-up is the best article of clothing for my particular body and style. I am partial to a few different shirts, starting with Ben Shermans:


Ben Sherman.


Ben Sherman is excellent for the shorter gentleman. The shirts don’t tend to be as long as many men’s shirts are.



Steven Alan also has great menswear–and hey!  they have a sample sale going on right now! (I promise, I do not work for Steven Alan). I want to emphasize that I buy almost all of this stuff on sale, because nice men’s shirts are expensive.

I stick with the narrow collar collegiate shirts from Steven Alan. Men’s shirt collars are often a little large for my neck, so I try to find shirts with narrower collars:


Steve Alan Narrow Colar Collegiate.


As I said, I have a bit of a uniform, but Steven Alan has other excellent lady-man appropriate options, too:


The left especially would be very nice for an androgynous gentleman.


My friend Karen swear by Burkman Bros. shirts:




And Thom recently introduced me to the wonder of Topman, whose shirts I love.


Topman peach horizontal stripe shirt.


I got this one a couple of weeks ago:


Also summery!


Topman also seems very aware that they have many non-cisgendered customers, which is nice.  I mean, really:


Nothing queer about that!


A word on cut:  though I am smaller than many men, I usually avoid slim cuts (e.g., at Topman). A slim-cut shirt will narrow towards the waist, but because I am shorter than many men, that waist will actually hit at my hips–exactly the place where I don’t want my shirt to narrow. A regular cut will be a little boxier, which, maybe counter-intuitively, tends to serve my body better.

This leads me to perhaps the most important point of all: tailoring. If you are a woman buying men’s clothes, things will often be too long, too wide, too something in some part of the garment. Getting your clothing tailored–yes, even your jeans– in fact, especially your jeans–will make you look a million times better, and allow you to wear things you might not otherwise feel good wearing.

There are a few companies now, like Marimacho, who actually make masculine clothing for a wider variety of bodies. These guys are great!




Also awesome!


Awesome again!

There wasn’t much, or really anything, like this when I was a lad.  Here’s hoping there is more and more in the future.

About Terry LaFrazia

Friend of a tailor. Interested in process and content.


  1. T. Royal Pulchritude

    For some really fly shoes, fluevog sells unisex shoes; men’s shoes that reach to a women’s 8/9 and some *dapper* womens shoes.

    my current flirtation:

  2. Pingback: Featherweight: on Muscle and Style «

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